


Do Not Pass Go

by sweetheartdean



Category: Supernatural
Genre: Angst, Bottom Dean, Dean Whump, Extremely Dubious Consent, Gen, John Winchester's A+ Parenting, M/M, Prostitute Dean, Prostitution, Unsafe Sex, good ole hookerfic, the sad three-legged puppy Dean of your dreams
Language: English
Status: Completed
Published: 2017-10-10
Updated: 2017-10-10
Packaged: 2019-01-10 01:34:26
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,995
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12288423
Author URL: https://archiveofourown.org/users/sweetheartdean/pseuds/sweetheartdean
Summary: The worst part is how the wad of cash Dad left behind keeps getting thinner and thinner and thinner. Like Sam would get if Dean didn’t get them more green.





	Do Not Pass Go

**Author's Note:**

> A huge thank you to the most lovely SleepyPercy for the betaing!

It’s always the same whenever Dad leaves for a hunt. He makes sure to check all the painted sigils and the salt lines. He gets his weapons ready, little deaths crammed inside barrels and glinting along the edges of knives. He picks his heavy leather coat off the rack that stands in the room-of-the-night’s corner. These things are always old and chipped. Once a hook couldn’t bear the weight of his coat and broke off in the middle of the night. All three Winchesters jumped up in alarm, weapons at the ready. Would've probably been hilarious if it hadn't been so serious, the three of them in various states of undress with weapons clutched in fingers, all good to go for a death match with a coat. 

If it was just Sam and Dean, they probably would have laughed. But not in front of Dad. Never in front of Dad. They take the good fight seriously as hell. At least, Dean does and Sam, mostly, is clever enough to follow his lead. Whenever Sam has a lapse in judgement, Dean jumps in between his father and brother, soothes all the sharp angles by placing himself between the muzzles of their stares and the bullets of their words. 

Next Dad places a hand on Dean’s shoulder, patting it a couple times. It’san unspoken watch-out-for-Sammy. Not that Dean needs to be told this. He will always watch out for Sammy, instruction or no instruction. 

Then, Dad hands Dean a wad of cash. A rubber band holds the rolled-up bank notes together. ‘S been like that ever since they were kids, money to keep Sam fed and a roof over their heads. Except that as time goes, the time he needs to spread the money over gets longer and longer, and the wad doesn’t get any thicker.

Sometimes they’re lucky. The hunt’s quick, and there’s even some money left over by the time the familiar roar of the Impala resounds outside the motel door. Dad never asks for it back, and Dean doesn’t hand it over. They might need it later.

Sometimes hunts drag on much longer than expected. Sam asks him every goddamn day whether he’s heard from Dad or not, and Dean has to say that _no, nothing yet, but I’m sure he’ll turn up soon, it’s Dad, after all_. But that’s not even the worst part. The worst part is how the wad keeps getting thinner and thinner and thinner. Like Sam would get if Dean didn’t get them more green. 

The receptionist expects him to pay up for the room. That’s kinda the main thing. He can steal food, no big deal, but the room payment is a bitch. 

The first time they run out of money, Dean pickpockets a wallet. He doesn’t do it again — too much of a risk. Stealing a wallet is a bigger deal than swiping a loaf of bread or two, and if he gets stuck in jail, no one’s gonna feed Sam while he’s gone.

The second time, he pawns a couple of their things. But they really don’t have much he can sell. 

The third time, it gets really bad. The stack is at an all-time low, and Sam and he have to hold their floral-wallpapered, scratched-floor fort. Somehow.

The sun slowly dips behind the horizon when Dean leaves the motel, promising Sam that he’ll make it back soon with some food. He wanders through the one-horse town they are stuck in before finally stopping at the local watering hole. Dean doesn’t have enough for the food, for the room, for any of it. Frankly, he’s this close to just pulling out his gun and shoving someone against the dingy wall in back alley to make them cough up some cash. His family’s been saving everyone and their mother’s sweet bacon for years and years without asking for as much as a thank you. They deserve at least enough to get by.

But that’s a line he cannot cross. It would feed Sam, yeah, but he’s not a robber. He’s not a killer. He kills the things that deserve to be dead, he pickpockets people, but actually pressing a barrel into an innocent person would be a point of no return.

So instead he goes inside, almost surprised he doesn’t get bounced, but the balding, tired guard at the door couldn’t give a rip about who comes in and who doesn’t. He barely dignifies Dean’s fake ID with a glance before walking aside. The booming, boisterous heat of the bar envelops him. A football match airs on a screen above the counter, a couple of guys eagerly rooting for the teams, loud conversations, the clinking of pool balls and the swooshing sounds of drinks being poured— 

Dean looks around the room, thinks to what he’s about to do and feels sick. Puke-his-guts-out level sick. 

He walks around the room, sliding his hand in his jeans’ pocket. Six coins and a bill are all he has, two dollars fifteen cents, and that’s nowhere near enough. There’s no plan B.

There’s a guy sitting alone, with a stocky build and a stubbled face that looks at him all too attentively. Which, hey, is lucky, Dean wouldn’t even know how to approach this whole thing otherwise. He can’t name what he’s about to do. It’s just means to an end, that’s all. Sam’s at home, alone and hungry. Even last night was kind of spotty food-wise. The gnawing emptiness in his own stomach keeps him alert, but also leaves him a little dizzy and weak at the knees.

If this guy picks a fight, Dean’s not in the best shape to throw a punch. He hopes he won’t have to. He readies himself for it either way, ‘cause shit tends to hit the fan.

“Hey.” Dean slides on the chair next to the guy and tries to look as pretty and likable as he can, his back straight and his eyes opened wide. He kind of regrets not wearing something more form-fitting. Army-green shirt and Salvation Army washed-out blue jeans with holes in them aren’t exactly a public pleaser in this new business he’s trying to break into. “Like what you see?”

The guy grunts, giving Dean an appreciative look-over. It’s not exactly sleazy, per se, but it does make Dean squirm on the inside a little.

What if he doesn’t like what Dean has to offer.

What if he does.

“That depends on what you’re selling here. And how much you’re asking, sweetheart.”

Sweetheart. That makes Dean feel like a character from a country song. He thinks, quick and desperate. To be honest, he has no fucking idea what the average price here is. And he’d much rather just blow the guy than slide his legs open, but he had never done that before. Dean’s gonna choke, or, worse, bite, and then he’s gonna get the shit kicked outta him for sure. 

“Two hundred for a go at my ass,” Dean finally says, fluttering his eyelashes like girls do. It would be enough to keep them in the room for three more days, with leftover cash for food. Dean props his elbow on the table and leans in, invading the man’s space. The guy smells like toothpaste and liquor, and he’s a little sweaty, but not enough for it to be completely gross. “Not spending the night and no kinky shit,” he adds right afterward. Better establish boundaries straightaway, right?

Fuck, Dean doesn’t know what he’s doing here, at all. But Sam’s waiting for him at home, salt on windows and doors. He’s probably doing homework now. Or watching TV. Thinking about Sammy helps, and Dean reaches out to put his fingers on the man’s bicep.

God, he wants to hurl, but he keeps on smiling instead. Feels like the smile got glued to his lips, and he’s gonna have to rip it off, like a band-aid, when he wants to stop. 

“What do you say, baby?” Dean whispers. Girls hit on him before. He hit on girls. Out of these two, he manages to concoct something in the middle.

“Two hundred? Your ass better be made of gold at that price.” The man clicks his tongue. “Hell, I’ll bite. But no rubber.”

Dean can’t help but widen his eyes on that. Risky shit. He’d walk away if he had any guarantee of finding anyone else buying tonight. 

“As long as you pull out,” he says finally. Talking about it feels just a bit better than pulling teeth without anesthesia. 

“Deal. I’ve got a room nearby.”

What if he’s renting in the same motel as they do, and Sam sees the two of them? But the town, after all, is big enough to have more than one place for a traveler to rest his bones. That’s lucky -- if any of this can be called lucky.

Dean’s heart thumps against his ribs, and he’s so, so very freaked. The guy could kick him out without paying. Could make him do shit Dean didn’t want. Could chop him up and keep his heart in a jar or some shit. But he might actually pay, and that’s enough for Dean to follow him through the motel’s hallway, his legs shaking slightly. He hopes they don’t give out. 

“What’s your name, kid?”

He looks up before blurting “Dean” out. Fucking awesome. ‘S not like Dean doesn’t give a fake name out all the time. But now, now he decides to be honest all of a sudden. 

“You do look like a Dean,” the guy answers and pulls him close by the waist. Dean leans on him and presses his hip close to the man’s, stomping down every instinct that tells him to do some stupid shit. Like twist that hand right behind the man’s back. “‘m Ray. Just so you know what to scream tonight.”

Fuck. It’s a common, lame pick-up line, but distorted by Dean’s panicking inner voice it sounds really fucking sinister. Dean swallows down something rising up his throat — can’t be food, there’s no food to come up — and takes a step in the room. It’s a normal, really bland motel room. He’s been to dozens of rooms like that all across the States. Didn’t get fucked in the ass for money in any, though. 

Ha. New experiences. 

“What are you waiting for?” Ray walks over to the bed — the bed Dean’s about to get screwed on. Dean’s fingers jump to his flannel’s buttons before he shrugs it off his shoulders. 

He takes note of where it fell, in case he needs to make a quick getaway. Then he walks over to the bed, hooking his thumbs in the belt loops of his jeans, swaying his hips a little. This Ray dude needs to get his money’s worth.

“C’mere,” the man says, placing his hands on Dean’s shoulders, and, before Dean knows it, he gets pulled in a kiss. It’s a bit sloppy, and the man’s tongue is way too invasive, but it’s not horrible, as far as kisses go. 

“Wanna know if the rest of you is as freckled as that face of yours.” Ray reaches out. He hoists up Dean’s shirt slowly, then grasps the black string with a golden amulet hanging off Dean’s neck. Dean is about to slap the hand away but slows his movement just in time, wrapping his fingers around Ray’s wrist instead. 

“I’d rather keep it on,” he says in a flat voice. 

“Suit yourself.” Ray shrugs, pushing Dean’s shirt up even more, exposing one of his nipples. He pinches his fingers around it, rolling it between his thumb and index finger. Dean arches his back a little belatedly. 

“Yeah, you like that?” 

“Mhhhm,” Dean croaks out. It’s weird, but, once again, not horrible. Ray tugs at his shirt before Dean gets the message and pulls it off, then throws it in the same direction as his flannel. Ray grasps his thigh, hooks it over his own leg, and dives in, kissing Dean’s neck and along his collarbone, the stubble prickling Dean’s skin. He doesn’t know if that’s considered as an extra, or if Ray’s actually doing him a solid and fluffing him up for the main action, and he doesn’t ask. If he closes his eyes, Ray can be anyone he wants. 

Even young Harrison Ford.

That works pretty smoothly, actually. Dean’s cock definitely twitches in interest when confronted with the image of Han Solo himself ravishing him like that. 

“Yeah,” Dean breathes out, looping his arm around not-Harrison-Ford’s shoulders. “Just like that.” The sounds he makes are enough to make blood rush to his face.

Ray finds Dean’s wrist and pulls his hand over to his denim-clad crotch. He’s already half-hard, and Dean begins obediently rubbing over the fabric in circles. 

Dean finally blinks his eyes open, confronted with the reality of things. This guy’s not porn-levels of hung, but he ain’t small, either, and this is gonna fucking hurt. He hopes Ray has lube stashed somewhere. Maybe Dean was supposed to carry it around, but the fact that he’d actually need it only had just dawned on him. 

So he’s being a little slow on the uptake today, sue him. 

“Take it all off,” Ray finally says, pulling away from where he was giving Dean beard-burn. Here it fucking comes. Dean’d much rather jump out that window, through the glass and all, but the promise of two hundred dollars beckons stronger than self-preservation instinct does. 

He stomps out of his jeans and takes his time getting out of his boxers, finally pulling them off when he hears an impatient noise come from Ray. His half-hard cock twitches again with Ray’s wolf-whistle.

“Lookin’ good, kid,” he says, and all Dean wants is to cover himself up again, now robbed of his last defense. ‘Sides, he’s not a kid. Well –maybe he is, compared to this guy, but he's only a few years shy of the legal drinking age. But Dean ain’t gonna argue. 

“Hands and knees.” Ray nods to the bed, and Dean obliges, surprised at how his shaking limbs seem to still support his weight in spite of the furious trembling in his arms. He stares at the headboard stubbornly, biting down on his lip. 

This isn’t what he is. This is just means to an end. Sam waits for him at home. 

Before he left the motel, Dean had put the rubber band that used to hold the bills together on his wrist, as a reminder of shit-being-bad. As if he needs that. Shit’s always bad. It just gets worse sometimes. Like right now.

A sharp smack to his ass jerks him back into the harsh reality. 

“Even your ass’s covered in freckles. You’re a pretty thing, alright,” Ray mumbles somewhere behind him, and Dean shivers. Yeah, he’s had steamy meetings with girls, rolling around in the backseat of the Impala and getting drunk on each other’s kisses. 

This, though, is fucked up something severe. 

There’s a sound of something popping open, and Dean lets out a stuttering breath when cold, lubed-up fingers graze his ass before trailing down to his entrance. 

It feels fuckin’ awful. Maybe, if he could relax, things would go easier, but he’s as far from relaxed as it gets.

“Kinda tight for a whore, aren’t ya?” Ray pants out. Fuck no. Once his jig’s up, Ray’s gonna leave him here, moneyless, yet plenty traumatized. 

Or else, he’s gonna find him even hotter, but that’s a risk Dean can’t take.

Dean bends his elbows, lying down, and presses his chest to the sheets, grey from the washes, buries his burning face in the pillow. He arches his back, presenting his ass for the taking, all submissive and fragile ‘n shit. The sheer fact that he has to stoop to this is making him almost wish he had enough guts to mug someone.

Fuck, he hates this. Every fucking second, and they haven’t even gotten to the main course yet.

The rubber band rolls against his wrist as Dean moves it, catching a couple of his arm hairs. It stings a little, but it’s a great wake-up call amongst the lemon-scented fabric softener fest he’s been burying his face in. Money-money-money. Must be funny. 

“Ain’t that a good thing, baby?” Dean breathes out, barely finding the words. 

“Sure is,” Ray agrees, screwing a second finger into him. “Fuck, you’re gorgeous.” 

The praise is probably supposed to make him better. It doesn’t. It makes him feel even worse, if anything.

He tries to think about Harrison Ford, but the moment’s kinda gone, so he thinks about Sam and tunes out until Ray’s hand is on the back of his neck, pressing him into the mattress.

So this is it. 

So tight. 

Dean tries to stay still. For two hundred, it’s the least he can do. 

So pretty.

He thinks about Sam, and then he thinks about fixing the Impala, about the way her engine works and how Dad said a throwaway line about, maybe, giving the car to Dean someday if he wants to bother with fixing the old thing up.

For her, Dean’s gonna get elbows-deep in machine oil.

Look at you, taking me. Little slut. 

He could’ve actually taken that guy on if he wanted. He wouldn’t know what hit him, and Dean would walk away with all of his cash, not just the bills he’s willing to throw on a barely legal hooker. But he doesn’t. He takes all of Ray’s cock instead, grunting and whimpering into the pillow desperately. 

There’s a hand squeezing his ass eagerly, and as much as Dean just wants to tune out, the reality is way too heavy for him to just push aside. 

So he bites down on his lip and tries to concentrate on that pain instead. 

“Hey, kid. Tell me how much you like this.”

And so Dean has no choice but to moan, taking cues from the pay-per-view pornos, and gush about the guy’s cock filling him to the brim, yeah, oh baby, I like it so much, fuck me like you mean it— he all but stutters through the first words, but then turns his hesitation into breathy moans, and it all goes smoother from there on. Soon enough, the man’s panting behind him, and it sounds horribly like— 

“You said you’ll pull out,” Dean says quickly.

“Not yet,” Ray says and just keeps going, like Dean hadn’t said anything. “Gonna get my money’s worth.” 

“I’m not kidding. Pull out.” 

“Not. Yet,” he punctuates the words with thrusts that shake Dean’s entire frame, and Dean tries to wriggle away, but the grip on his neck tightens, and he just fucking knows all his struggles are just gonna get him impaled on the cock even further.

Fuck. Fuck. He’s gonna get infected with some horrible shit, isn’t he? 

And then there’s the last thrust and Dean gets pulled up a little and tossed onto the mattress again mere seconds before something warm and sticky hits his lower back. Ray reaches around, giving Dean’s dick a couple of lackluster tugs out of the goodness of his heart. Dean doesn’t need a lot here, arching up with a weak cry. 

The amulet, the one Sam gave him, jams into the hollow between his ribs, and it makes him wake up from the daze he’s in. Dean looks over his shoulder before sitting up. Vomiting can wait until he’s home.

“Told you I’d pull out. What were you being all freaked for?” Ray gives Dean a once-over. His dick’s still glistening with come, the come that’s smeared across Dean’s back right now. Dean scowls. “You’re so jittery. You’d think you’re doing this for the first time.” 

“Pay up.”

“You _were _doing this for the first time.”__

“None of your fucking business. Gimme the damn money,” Dean all but snarls. Probably, that’s not how hookers are supposed to act with paying customers, but he’s at his wit’s end.

“Thought as much. Were you a virgin?”

“Money,” Dean repeats like a broken record and extends his hand. Money. Food. Feed Sammy. He needs to think about that and that only or he’ll lose his fucking marbles right here and now.

“Yeah, a virgin, alright. Y’know, kiddo, you shouldn’t be doing this. You won’t be that young and tight forever. And trusting people like that ain’t gonna get you anywhere in this business.”

“Spare me the fucking lecture, dude,” Dean says, and then Ray finally pulls out his wallet and presses several bills into Dean’s hand, closing his fingers over him. 

“A little extra. I did pop your cherry, after all,” Ray grins and leans in to kiss Dean again, which he dodges. “Hey— c’mon, gimme a goodbye kiss, Dean.”

“Fuck off,” Dean snaps, jumping off the bed— fuck-fuck-fuck, it hurts. Now that he had his cash, he’s done with this Ray dude, with this motel, with all of it. He picks up his clothes and dresses as quickly as he can. He feels Ray’s hungry eyes on his lower back. 

“Ha. So, it’s all about the green for you already? Didn’t take you long to become a greedy whore. Maybe you _should_ be doing this.” 

Dean pulls in a sharp breath and flips Ray off before walking out of that room as fast as he’s able.

He only checks how much Ray gave him when he’s far enough from the motel to not be plagued with thoughts of Ray catching up with him and making him go at it again. 

It’s four fifties and one twenty, and the twenty is what leaves Dean on the edge of a breakdown next to a 7-11. 

Twenty dollars. That’s how much being unsullied goes for these days. 

Dean doesn’t break down, after all. He rolls the bills up and wraps the rubber band around them instead. He’s not a whore. He’s not a whore. He’s not a fucking whore. It’s just means to an end, ‘s all.

Dean asks for the sandwiches he buys to be wrapped separately, just ‘cause he really doesn’t want to be touching anything that Sam’s gonna be eating right now. He feels so dirty, inside and out. Wants to scrub his skin until it’s red and raw.

That Ray dude was as honest with him as he could’ve been, and Dean wants to hate him, but he can’t. The only person to blame for how sick he feels is himself. 

Sam meets him on the doorstep, wide-eyed and scared.

“Dean! Where have you been?!” he gasps out, and Dean frowns. 

“Hey, it’s school night. What the hell are you doing up?” he says in his stern parent voice and hopes he doesn’t look too much like someone who just got fucked for money.

“I— I was waiting for you! I didn’t know where you went, and you wouldn’t pick your phone. Geez, Dean. You scared me!”

“Relax, Sammy. I’ve been drumming up some cash. Here, take these.” Dean thrusts— no, poor choice of words — _hands_ the sandwiches over, making sure he doesn’t touch Sam’s hand with his. He walks in, and, okay, he’s limping a little, and there’s no way Sam didn’t notice it. 

“What were you doing? Where?”

“Hustling pool. Had to take someone outside. You should see the other guy.” Specifically, how hard he came. 

“But—”

“Get in bed, Sam,” Dean snaps. “Now.”

“Dean—”

“What?”

Sam looks at Dean’s hands. Which don’t have bruised knuckles or anything. 

“Sam, uh...”

“I’m just glad you weren’t hurt too bad. I’m sure that dude knows better than to mess with you now.” 

Dean smiles, gratefully. 

“You bet.” He falls silent for a bit before walking over to the bathroom. “I’m gonna hit the shower.”

“Yeah, sure. And, uh, Dean?” Dean turns around. “Thanks.”

The heavy coat finds its place on the hook three days later.

Dad places his hand on Dean’s shoulder.

Good job watching out for Sammy, son.


End file.
